Electroluminescent device

ABSTRACT

Disclosed are electroluminescent devices that comprise organic layers that contain triazine compounds. The triazine compounds are suitable components of blue-emitting, durable, organo-electroluminescent layers. The electroluminescent devices may be employed for full color display panels in, for example, mobile phones, televisions and personal computer screens.

The present invention relates to organo-electroluminescent (EL) devices,in particular EL devices that comprise durable, blue-emittingorgano-electroluminescent layers. The organo-electroluminescent layerscomprise certain triazine compounds.

The present invention is aimed at an electroluminescent devicecomprising an organic light-emitting layer that contains at least oneblue-emitting triazine compound.

U.S. Pat. No. 6,352,791 relates to an electroluminescent arrangement,comprising at least two electrodes, and a light emitting layer systemincluding at least one emitter layer and at least oneelectron-conducting layer, wherein the at least one electron-conductinglayer does not emit light and includes one triazine compound, such as,for example,

U.S. Pat. No. 6225467 is directed to organic electroluminescent (EL)devices, which contain an electron transport component comprised oftriazine compounds, such as, for example,4,6-tris(4-biphenylyl}1,3,5-triazine,2,4,6-tris[4-(4′-methylbiphenylyl)]-1,3,5-triazine,2,4,6-tris]4′-tert-butylbiphenylyly)-3,5-triazine,2,4,6-tris[-(3′,4′-dimethylbiphenylyl)]-1,3,5-triazine,2,4,6-tris[4-4′-methoxybiphenylyl)]-1,3,5-triazine,2,4,6-tris[4-3′-methoxybiphenylyl)]-1,3,5-triazine,2,4-bis(4-biphenylyl)-6-phenyl-1,3,5-triazine and2,4-bis(4-biphenylyl)-6-m-tolyl-1,3,5-triazine.

EP-A-1,202,608 relates to an electroluminescent arrangement, wherein ahost material constituting the hole transporting layer is a compound offormula

EP-A-1,013,740 relates to an electroluminescent element, wherein amongothers the following compound can be used as EL material:

It is the object of the present invention to provide a light emittingelement with excellent light emitting characteristics and durability.

Accordingly the present invention relates to an electroluminescentdevice comprising an anode, a cathode and one or a plurality of organiccompound layers sandwiched therebetween, in which said organic compoundlayers comprise a triazine compound of formula

X and Y are independently of each other an aryl group or a heteroarylgroup, especially a group of formula

R¹¹, R¹¹′, R¹², R¹²′, R¹³, R¹³+, R¹⁵, R¹⁵′, R¹⁶, R¹⁶′, R¹⁷, R¹⁷′, R⁴¹,R⁴¹′, R⁴², R⁴²′, R⁴², R⁴², ′, R⁴⁴, R⁴⁴′, R⁴⁵, R⁴⁵′, R⁴⁸ , R⁴⁸′, R⁴⁷ andR⁴⁷′ are independently of each other H, E, C₆-C₁₈aryl; C₆-C₁₈aryl whichis substituted by G; C₁-C₁₈alkyl; C₁-C₁-C₁₈-alkyl which is substitutedby E and/or interrupted by D; C₇C₁₈aralkyl; or C₇-C₁₈aralkyl which issubstituted by G; or

R¹¹′ and R¹², R¹²′ and R¹³, R¹⁵and R¹⁶, R¹⁶′ and R¹⁷, R⁴⁴′ and R⁴⁸and/or R⁴⁵′ and R⁴⁷ are each a divalent group L¹ selected from an oxygenatom, an sulfur atom, >CR¹⁸R¹⁹>SiR¹⁸R¹⁹, or

R¹⁸ and R¹⁹⁵ are independently of each other C₁-C₁₈alkyl; C₁-C₁₈alkoxy,C₆-C₁₈aryl; C₇-C₁₈aralkyl;

R¹¹ and R¹¹′, R¹² and R¹²′, R¹³ and R¹³′, R¹⁴, R¹⁴ and R¹⁵ , R¹⁵, R¹⁵′,R¹⁶, R¹⁶′, R¹⁷ ′ and R¹⁷, R⁴¹ and R⁴¹′, R⁴² and R⁴²′, and R⁴³, R⁴¹′, andR⁴³, R⁴⁴ and R⁴⁴′, R⁴⁵ and R⁴⁵′, R⁴⁶ and R^(46′, R) ⁴⁷ and R⁴⁷′, R⁴⁸′and R⁴⁸ and/or R⁴⁷′ and R⁴⁸ are each a divalent group

R³⁰, R³¹, R³², R³², R⁴⁹ and R⁵⁰ are independently of each other H,C₁-C₁₈alkyl; C₁-C₁₈alkyl, which is substituted by E and/or interruptedby D; E; C₆-C₁₈aryl; C₆-C₁₈aryl, which is substituted by E;

R¹⁴ is H, C₂-C₃₀heteroaryl, C₂-C₃₀heteroaryl, which is substituted by G,C₆-C₃₀aryl, or C₆-C₃₀aryl, which is substituted by G, C₁-C₁₈alkyl; orC₁-C₁₈alkyl which is substituted by E and/or interrupted by D;especially

wherein R²¹, R²², R²³, R²⁴, R²⁵, R²⁶ and R²⁷ are independently of eachother H, E, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by E and/orinterrupted by D; E; C₇-C₁₈aralkyl; C₇-C₁₈aralkyl which is substitutedby G;

R⁴³ and R⁴⁸ are independently of each other H, E; C₁-C₁₈alkyl;C₁-C₁₈alkyl, which is substituted by E and/or interrupted by D;C₂-C₃₀heteroaryl; C₂-C₃₀heteroaryl, which is substituted by G,C₇-C₁₈aralkyl; or C₇-C₁₈aralkyl which is substituted by G;

D is —CO—; —COO—; —OCO—; —S—; —SO—; —SO₂—; —O—, —NR⁵—; SiR⁶¹R⁶²—;—POR⁵—; —CR⁶³═CR⁶⁴—; or —C═C—;

E is —OR⁵; —SR⁶; —NR⁵R⁶; —COR⁸; —COOR⁷; —OCOOR⁷, —CONR⁵R⁶; —CN; orhalogen;

G is E, or C₁-C₁₈alkyl,

wherein R⁵ and R⁶ are independently of each other C₆-C₁₈aryl; C₆-C₁₈arylwhich is substituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy; or C₁-C₁₈alkyl whichis interrupted by —O—; or

R⁵ and R⁶ together form a five or six membered ring, in particular

R⁷ is C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl,C₁-C₁₈alkoxy; or C₁-C₁₈allyl which is interrupted by —O—;

R⁸ is C₇-C₁₂alkylaryl; C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is interruptedby —O—;

R⁶¹ and R⁶² are independently of each other C₆-C₁₈aryl; C₆-C₁₈aryl whichis substituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy; or C₁-C₁₈alkyl which isinterrupted by —O—, and

R⁶³ and R⁶⁴ are independently of each other H, C₆-C₁₈aryl; C₆-C₁₈arylwhich is substituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy; or C₁-C₁₈alkyl whichis interrupted by —O—.

In general, the triazine compound or compounds emit light below about520 nm, in particular between about 380 nm and about 520 nm.

The triazine compound or compounds have a NTSC coordinate of betweenabout (0.12, 0.05) and about (0.16, 0.10), preferably a NTSC coordinateof about (0.14, 0.08).

The triazine compound or compounds have a melting point above about 150°C., preferably above about 200° C. and most preferred above about 250°C.

To obtain organic layers of this invention with the proper T_(g), orglass transition temperature, it is advantageous that the presentorganic compounds have a glass transition temperature greater than about100° C., for example greater than about 110° C., for example greaterthan about 120° C., for instance greater than about 130° C.

The electroluminescent devices of the present invention are otherwisedesigned as is known in the art, for example as described in U.S. Pat.Nos. 5,518,824, 6,225,467, 6,280,859, 5,629,389, 5,486,406, 5,104,740,5,116,708 and 6,057,048, the relevant disclosures of which are herebyincorporated by reference.

For example, organic EL devices contain one or more layers such as:

substrate; base electrode; hole-injecting layer; hole transportinglayer; emitter layer; electron-transporting layer; electron-injectinglayer; top electrode; contacts and encapsulation.

This structure is a general case and may have additional layers or maybe simplified by omitting layers so that one layer performs a pluralityof tasks. For instance, the simplest organic EL device consists of twoelectrodes which sandwich an organic layer that performs all functions,including the function of light emission.

A preferred EL device comprises in this order:

(a) an anode,

(b) a hole injecting layer and/or a hole transporting layer,

(c) a light-emitting layer,

(d) optionally an electron transporting layer and

(e) a cathode.

In particular, the present organic compounds function as light emittersand are contained in the light emission layer or form the light-emittinglayer.

The light emitting compounds of this invention exhibit intensefluorescence in the solid state and have excellentelectric-field-applied light emission characteristics. Further, thelight emitting compounds of this invention are excellent in theinjection of holes from a metal electrode and the transportation ofholes; as well as being excellent in the injection of electrons from ametal electrode and the transportation of electrons. They areeffectively used as light emitting materials and may be used incombination with other hole transporting materials, other electrontransporting materials or other dopants.

The organic compounds of the present invention form uniform thin films.The light emitting layers may therefore be formed of the present organiccompounds alone.

Alternatively, the light-emitting layer may contain a knownlight-emitting material, a known dopant a known hole transportingmaterial or a known electron transporting material as required. In theorganic EL device, a decrease in the brightness and life caused byquenching can be prevented by forming it as a multi-layered structure.The light-emitting material, a dopant, a hole-injecting material and anelectron-injecting material may be used in combination as required.Further, a dopant can Improve the light emission brightness and thelight emission efficiency, and can attain the red or blue lightemission. Further, each of the hole transporting zone, thelight-emitting layer and the electron transporting zone may have thelayer structure of at least two layers. In the hole transporting zone inthis case, a layer to which holes are injected from an electrode iscalled “hole-injecting layer”, and a layer which receives holes from thehole-injecting layer and transport the holes to a light-emitting layeris called “hole transporting layer”. In the electron transporting zone,a layer to which electrons are injected from an electrode is called“electron-injecting layer”, and a layer which receives electrons fromthe electron-injecting layer and transports the electrons to alight-emitting layer is called “electron transporting layer”. Theselayers are selected and used depending upon factors such as the energylevel and heat resistance of materials and adhesion to an organic layeror metal electrode.

The light-emitting material or the dopant which may be used in thelight-emitting layer together with the organic compounds of the presentinvention includes for example anthracene, naphthalene, phenanthrene,pyrene, tetracene, coronene, chrysene, fluorescein, perylene,phthaloperylene, naphthaloperylene, perinone, phthaloperinone,naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene, coumarine,oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine,cyclopentadiene, quinoline metal complex, aminoquinoline metal complex,benzoquinoline metal complex, imine, diphenylethylene, vinyl anthracene,diaminocarbazole, pyran, thiopyran, polymethine, merocyanine, animidazole-chelated oxynoid compound, quinacridone, rubrene, andfluorescent dyestuffs for a dyestuff laser or for brightening.

The triazine compounds of the present invention and the above compoundor compounds that can be used In a light-emitting layer may be used inany mixing ratio for forming a light-emitting layer. That is, theorganic compounds of the present invention may provide a main componentfor forming a light-emitting layer, or they may be a doping material inanother main material, depending upon a combination of the abovecompounds with the organic compounds of the present invention.

The hole-injecting material is selected from compounds which are capableof transporting holes, are capable of receiving holes from the anode,have an excellent effect of injecting holes to a light-emitting layer ora light-emitting material, prevent the movement of excitons generated ina light-emitting layer to an electron-injecting zone or anelectron-injecting material and have the excellent capability of forminga thin film. Suitable hole-injecting materials include for example aphthalocyanine derivative, a naphthalocyanine derivative, a porphyrinderivative, oxazole, oxadiazole, triazole, imidazole, imidazolone,imidazolthione, pyrazoline, pyrarolone, tetrahydroimidazole, oxazole,oxadiazole, hydrazone, acylhydrazone, polyarylalkane, stilbene,butadiene, benzidine type triphenylamine, styrylamine typetriphenylamine, diamine type triphenylamine, derivatives of these, andpolymer materials such as polyvinylcarbazole, polysilane and anelectroconducting polymer.

In the organic EL device of the present invention, the hole-injectingmaterial which is more effective is an aromatic tertiary aminederivative or a phthalocyanine derivative. Although not speciallylimited, specific examples of the tertiary amine derivative includetriphenylamine, tritolylamine, tolyldiphenylamine,N,N′-diphenyl-N,N′-(3-methylphenyl)-1,1-biphenyl-4,4′-diamine,N,N,N′,N′-tetra(4-methylphenyl)-1,1′-phenyl4,4′-diamine,N,N,N′,N′-tetra(4-methylphenyl)1,1′-biphenyl-4,4′-diamine,N,N′-diphenyl-N,N′-dl(1-naphthyl)1,1′-biphenyl-4,4′-diamine,N,N′-di(methylphenyl)-N,N′-di(4-n-butylphenyl)phenanthrene-9,10-diamine,4,4′,4″-tris(3-methylphenyl)-N-phenylamino)triphenylamine,1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, and oligomers or polymershaving aromatic tertiary amine structures of these.

Although not specially limited, specific examples of the phthalocyanine(Pc) derivative include phthalocyanine derivatives or naphthalocyaninederivatives such as H₂Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc,CIAIPc, CIGaPc, CIInPc, CISnPc, Cl₂SiPc, (HO)AIPc, (HO)GaPc, VOPc,TiOPc, MoOPc, and GaPc-O-GaPc.

The hole transporting layer can reduce the driving voltage of the deviceand improve the confinement of the injected charge recombination withinthe triazine light emitting layer. Any conventional suitable aromaticamine hole transporting material described for the hole-injecting layermay be selected for forming this layer.

A preferred class of hole transporting materials is comprised of4,4′-bis(9-carbazolyl)-1,1′-biphenyl compounds of the formula

wherein R⁶¹ and R⁶² is a hydrogen atom or an C₁-C₃alkyl group; R⁶³through R⁶⁶ are substituents independently selected from the groupconsisting of hydrogen, a C₁-C₆alkyl group, a C₁-C₆alkoxy group, ahalogen atom, a dialkylamino group, a C₆-C₃₀aryl group, and the like.Illustrative examples of 4,4′-bis(9-carbazolyl)-1,1′-biphenyl compoundsinclude 4,4′-bis(9-carbazolyl)-1,1′-biphenyl and4,4′-bis(3-methyl-9-carbazolyl)-1,1′-biphenyl, and the like. Theelectron transporting layer is not necessarily required for the presentdevice, but is optionally and preferably used for the primary purpose ofImproving the electron injection characteristics of the EL devices andthe emission uniformity. Illustrative examples of electron transportingcompounds, which can be utilized in this layer, include the metalchelates of 8-hydroxyquinoline as disclosed in U.S. Pat. Nos. 4,539,507,5,151,629, and 5,150,006, the disclosures of which are totallyincorporated herein by reference.

Although not specially limited, specific examples of the metal complexcompound include lithium 8-hydroxyquinolinate, zincbis(8-hydroxyquinolinate), copper bis(8-hydroxyquinolinate), manganesebis(8-hydroxyquinolinate), aluminum tris(8-hydroxyquinolinate), aluminumtris(2-methyl-8-hydroxyquinolinate), gallium tris(8-hydroxyquinolinate),beryllium bis(10-hydroxybenzo[h]quinolinate), zincbis(10-hydroxybenzo[h]quinolinate), chlorogalliumbis(2-methyl-8-quinolinate), galliumbis(2-methyl-8-quinolinate)(o-cresolate), aluminumbis(2-methyl-quinolinate)(1-naphtholate), galliumbis(2-methyl-8-quinolinate)(2-naphtholate), galliumbis(2-methyl8-quinolinate)phenolate, zincbis(o-(2-benzooxazolyl)phenolate), zincbis(o-(2-benzothiazolyl)phenolate) and zincbis(o-(2-benzothiazolyl)phenolate). The nitrogen-containingfive-membered derivative is preferably an oxazole, thiazole,thiadiazole, or triazole derivative. Although not specially limited,specific examples of the above nitrogen-containing five-memberedderivative include 2,5-bis(1-phenyl)1,3,4-oxazole,1,4-bis(2-(4-methyl-5-phenyloxazolyl)benzene, 2,5-bis(1-phenyl)1,3,4-thiazole, 2,5-bis(1-phenyl)-1,3,4-oxadiazole,2-(4-tert-butylphenyl)-5-(4″-biphenyl)1,3,4-oxadiazole,2,5-bis(i-naphthyl)1,3,4-oxadiazole,1,4-bis[2-(5-phenyloxadiazolyl)]benzene, 1,4-bis[2-(5-phenyloxadiazolyl)tert-butylbenzene],2-(4′-tert-butylphenyl)-5-(4-biphenyl)-1,3,4-thiadiazole,2,5-bis(1-naphthyly)-1,3,4-thiadiazole,1,4-bis[2-(5-phenylthiazolyl)]benzene,2-(4′-tert-butylphenyl-)5-4″-biphenyl)-1,3,4-triazole,2,5-bis(1-naphthyl)-3,4-triazole and1,4-bis[2-(5-phenyltriazolyl)]benzene. Another class of electrontransport materials are oxadiazole metal chelates, such asbis[2-(2-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazolato]beryllium;bis[2-(2-hydroxyphenyl)-5-(1-naphthyl)-1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-(1-naphthyl)-1,3,4-oxadiazolato]beryllium;bis[5-biphenyl-2-(2-hydroxyphenyl)-1,3,4-oxadiazolato]zinc;bis[5-biphenyl-2-2-hydroxyphenyl)-1,3,4-oxadiazolato]beryllium;bis(2-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazolato]lithium;bis[2-(2-hydroxyphenyl)-5-p-tolyl-1,3,4-oxadiazolato]zinc; bis2-2-hydroxyphenyl)5-p-tolyl-1,3,4oxadiazolato]beryllium;bis[5-(p-tert-butylphenyl)2-(2-hydroxyphenyl)-1,3,4-oxadiazolato]zinc;bis[5-(p-tert-butylphenyl)-2-(2-hydroxyphenyl)-1,3,4-oxadiazolato]beryllium;bis[2-(2-hydroxyphenyl)-5-(3-fluorophenyl)-1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-(4fluorophenyl)1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-(4-fluorophenyl)-1,3,4-oxadiazolato]beryllium;bis[5-4-chlorophenyl)-2-(2-hydroxyphenyl)1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazolato]zinc;bis[2-2-hydroxy4-methylphenyl)-5-phenyl-1,3,4-oxadiazolato]zinc;bis[2-.alpha.-2-hydroxynaphthyl5-phenyl-1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-p-pyridyl-1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxyphenyl-5-p-pyridyl-1,3,4-oxadiazolato]beryllium;bis[2-(2-hydroxyphenyl5-2-thiophenyl)-1,3,4-oxadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-phenyl-1,3,4,-thiadiazolato]zinc;bis[2-(2-hydroxyphenyl)-5-phenyl-1,3,4-thiadiazolato]beryllium;bis[2-(2-hydroxyphenyl)-5-(1-naphthyl)-1,3,4-thiadiazolato]zinc, andbis[2-(2-hydroxyphenyl)5-(1-naphthyl)-1,3,4-thiadiazolato]beryllium, andthe like.

In the organic EL device of the present invention, the light-emittinglayer may contain, in addition to the light-emitting organic material ofthe present invention, at least one of other light-emitting material,other dopant, other hole-injecting material and other electron-injectingmaterial. For improving the organic EL device of the present inventionin the stability against temperature, humidity and ambient atmosphere, aprotective layer may be formed on the surface of the device, or thedevice as a whole may be sealed with a silicone oil, or the like.

The electrically conductive material used for the anode of the organicEL device is suitably selected from those materials having a workfunction of greater than 4 eV. The electrically conductive materialincludes carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten,silver, gold, platinum, palladium, alloys of these, metal oxides such astin oxide and indium oxide used for ITO substrates or NESA substrates,and organic electroconducting polymers, such as polythiophene andpolypyrrole.

The electrically conductive material used for the cathode is suitablyselected from those having a work function of smaller than 4 eV. Theelectrically conductive material includes magnesium, calcium, tin, lead,titanium, yttrium, lithium, ruthenium, manganese, aluminum and alloys ofthese, while the electrically conductive material shall not be limitedto these. Examples of the alloys include magnesium/silver,magnesium/indium and lithium/aluminum, while the alloys shall not belimited to these. Each of the anode and the cathode may have a layerstructure formed of two layers or more as required.

For the effective light emission of the organic EL device, at least oneof the electrodes is desirably sufficiently transparent in the lightemission wavelength region of the device. Further, the substrate isdesirably transparent as well. The transparent electrode is producedfrom the above electrically conductive material by a deposition methodor a sputtering method such that a predetermined light transmittance issecured. The electrode on the light emission surface side has forinstance a light transmittance of at least 10%. The substrate is notspecially limited so long as it has adequate mechanical and thermalstrength and has transparency. For example, it is selected from glasssubstrates and substrates of transparent resins such as a polyethylenesubstrate, a polyethylene terephthalate substrate, a polyether sulfonesubstrate and a polypropylene substrate.

In the organic EL device of the present invention, each layer can beformed by any one of dry film forming methods such as a vacuumdeposition method, a sputtering method, a plasma method and an ionplating method and wet film forming methods such as a spin coatingmethod, a dipping method and a flow coating method. The thickness ofeach layer is not specially limited, while each layer is required tohave a proper thickness. When the layer thickness is too large,inefficiently, a high voltage is required to achieve predeterminedemission of light. When the layer thickness is too small, the layer isliable to have a pinhole, etc., so that sufficient light emissionbrightness is hard to obtain when an electric field is applied. Thethickness of each layer is for example in the range of from about 5 nmto about 10 μm, for instance about 10 nm to about 0.2 μm.

In the wet film forming method, a material for forming an intended layeris dissolved or dispersed in a proper solvent such as ethanol,chloroform, tetrahydrofuran and dioxane, and a thin film is formed fromthe solution or dispersion. The solvent shall not be limited to theabove solvents. For improving the film formability and preventing theoccurrence of pinholes in any layer, the above solution or dispersionfor forming the layer may contain a proper resin and a proper additive.The resin that can be used includes insulating resins such aspolystyrene, polycarbonate, polyarylate, polyester, polyamide,polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylateand cellulose, copolymers of these, photoconductive resins such aspoly-N-vinylcarbozole and polysilane, and electroconducting polymerssuch as polythiophene and polypyrrole. The above additive includes anantioxidant, an ultraviolet absorbent and a plasticizer.

When the light-emitting organic material of the present invention isused in a light-emitting layer of an organic EL device, an organic ELdevice can be improved in organic EL device characteristics such aslight emission efficiency and maximum light emission brightness.Further, the organic EL device of the present invention is remarkablystable against heat and electric current and gives a usable lightemission brightness at a low actuation voltage. The problematicdeterioration of conventional devices can be remarkably decreased.

The organic EL device of the present invention has significantindustrial values since It can be adapted for a flat panel display of anon-wall television set, a flat light-emitting device, a light source fora copying machine or a printer, a light source for a liquid crystaldisplay or counter, a display signboard and a signal light.

The material of the present invention can be used in the fields of anorganic EL device, an electrophotographic photoreceptor, a photoelectricconverter, a solar cell, an image sensor, dye lasers and the like.

The triazine compounds of formula I are novel. Hence, a further subjectof the present invention is directed to triazine compounds of formula

X and Y are independently of each other an aryl group or a heteroarylgroup, especially a group of formula

R¹¹, R¹¹′, R¹², R¹²′, R¹³, R¹³′, R¹⁵, R¹⁵′, R¹⁶, R¹⁶′, R¹⁷, R¹⁷′, R⁴¹,R⁴¹′, R⁴², R⁴²′, R⁴⁵, R⁴⁵′, R⁴⁵, R⁴⁵′, R⁴⁶, R⁴⁶′, R⁴⁷ and R⁴⁷′ areindependently of each other H, E, C₆-C₁₈aryl; C₆-C₁₈aryl which issubstituted by G; C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by Eand/or interrupted by D; C₇-C₁₈aralkyl; or C₇-C₁₈aralkyl which issubstituted by G; or

R¹¹′ and R¹², R¹²′ and R¹³, R¹⁵′ and R¹⁶, R¹⁶′ and R¹⁷, R⁴⁴′ andR⁴⁸and/or R⁴⁶′ and R⁴⁷are each a divalent group L¹ selected from anoxygen atom, an sulfur atom, >CR¹⁸R¹⁹>SiR¹⁸R¹⁹, or

R¹⁸ and R¹⁹ are independently of each other C₁-C₁₈alkyl; C₁-C₁₈alkoxy,C₅-C₁₈aryl; C₇-C₁₈aralkyl;

R¹¹ and R¹¹′, R¹² and R¹²′, R¹³, and R¹³′, R¹³′, and R¹⁴, R¹⁴ and R¹⁵,R¹⁶ and R¹⁵′, and R¹⁶ and R¹⁸′, R¹⁷ and R¹⁷, R⁴¹ and R⁴¹′, R⁴² and R⁴²′and R⁴³, R⁴¹′ and R⁴³, R⁴⁴ and R⁴⁴′, R⁴⁵ and R⁴⁶′, R⁴⁶ and R⁴⁶′, R⁴⁷ andR⁴⁷′, R⁴⁶′ and R⁴⁸ and/or R⁴⁷ and R⁴⁸ are each a divalent group

R³⁰, R³¹, R³², R³³, R⁴⁹ and R⁵⁰ are independently of each other H,C₁-C₁₈alkyl; C₁-C₁₈alkyl, which is substituted by E and/or interruptedby D; E; C₆-C₁₈aryl; C₆-C₁₈aryl, which is substituted by E;

R¹⁴ is H, C₂-C₃₀heteroaryl, C₂-C₃₀ oheteroaryl, which is substituted byG. C₆aryl, or C₈-C₃₀aryl, which is substituted by G, C₁-C₁₈alkyl; orC₁-C₁₈alkyl which is substituted by E and/or interrupted by D;especially

wherein R²¹, R²², R²⁴, R²⁵, R²⁶ and R²⁷ are independently of each otherH, E, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by E and/orinterrupted by D; E; C₇-C₁₈aralkyl; C₇-C₁₈aralkyl which is substitutedby G;

R⁴³ and R⁴⁸ are independently of each other H, E; C₁-C₁₈alkyl;C₁-C₁₈alkyl, which is substituted by E and/or interrupted by D;C₂-C₃₀heteroaryl; C₂-C₃₀heteroaryl, which is substituted by G,C₇-C₁₈aralkyl; or C₇-C₁₈aralkyl which is substituted by G;

D is —CO—; —COO—; —OCOO—; —S—; —SO—; —SO₂—; —O—; —NR⁵—; SiR⁶¹R⁶²;—POR⁵—; —CR⁶³═CR⁶⁴—; or —C═C—;

E is —OR⁵; —SR⁵; —NR⁵R⁶; —COR⁸; —COOR⁷; —OCOOR⁷, —CONR⁵R⁶; —CN; orhalogen; G is E, or C₁-C₁₈alkyl,

wherein R⁵ and R⁸ are independently of each other C₆-C₁₈aryl; C₆-C₁₈arylwhich is substituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy; or C₁-C₁₈alkyl whichis interrupted by —O—; or

R⁵ and R⁶ together form a five or six membered ring, in particular

R⁷ is C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl,C₁-C₈alkoxy; or C₁-C₁₈alkyl which is interrupted by —O—;

R⁸ is C₇-C₁₂alkylaryl; C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is interruptedby —O—;

R⁶¹ and R⁶² are independently of each other C₆-C₁₈aryl; C₆-C₁₈aryl whichis substituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy; or C₁-C₁₈alkyl which isinterrupted by —O—, and

R⁶³ and R64 are independently of each other H, C₆-C₁₈aryl; C₆-C₁₈arylwhich is substituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy, or C₁-C₁₈alkyl whichis interrupted by —O—.

W is preferably a group of formula

R¹³, R¹³′, R¹⁵ and R¹⁵′ are H and R²⁰ is H, especially

R¹³ and R¹⁵ are H, R¹³′ and R¹⁵ are independently of each other H,C₁-C₈alkyl, or C₁-C₈alkoxy, and R²⁰ is H, C₁-C₁alkyl, or C₁-C₈alkoxy; or

R¹³, R¹⁵ and R¹⁵′ are H, and R¹³′ and R²⁰ are

R²⁰, R¹⁵ and R¹⁵′ are H, and R¹³ and R³′ are

wherein

R³⁰, R³¹, R³² and R³³ are H, C₁-C₈alkyl, or C₁-C₈alkoxy, and

X and Y are as defined above.

According to the present invention at least W, preferably W and Y, mostpreferred W, Y and

X are a group of formula

Accordingly, in one preferred embodiment of the present invention thetriazine compound is a compound of formula I, wherein W and Y areindependently of each other a group of formula

X is a group of formula

wherein R¹¹, R¹¹′, R¹², R¹²′, R¹³, R¹³′, R¹⁴, R¹⁵, R¹⁵′, R¹⁶, R¹⁶′, R¹⁷,R¹⁷′, R⁴¹, R⁴¹′, R⁴², R⁴²′, R⁴⁴, R⁴⁴′, R⁴⁵, R⁴⁵′, R⁴⁶, R⁴⁶′, R⁴⁷, R⁴⁷′,R⁴³ and R⁴⁸ are as defined above, and are especially H, C₁-C₈alkyl,C₁-C₈alkoxy, or phenyl.

R¹¹, R¹¹′, R¹², R¹²′, R¹³, R¹³′, R¹⁵, R¹⁵′, R¹⁶, R¹⁶′, R¹⁷ and R¹⁷′,R⁴¹, R⁴¹′, R⁴², R⁴²′, R⁴⁴, R⁴⁴′, R⁴⁵, R⁴⁵′, R⁴⁶, R⁴⁶′, R⁴⁷, and R⁴⁷′0 aswell as R¹⁴, R43, and R45 are preferably independently of each other H,E; or C₁-C₈alkyl, especially H. C₁-C₄alkyl, C₁-C₄alkoxy, or phenyl;wherein E is —OR⁶; —SR⁵; —NR⁵R⁸; —COR⁸; —COOR⁷; —CONR⁵R⁶; —CN; —OCOOR⁷;or halogen; wherein R⁵ and R⁶ are independently of each otherC₆-C₁₂aryl, or C₁-C₈alkyl;

R⁷ is C₇-C₁₂ alkylaryl, or C₁-C₈alkyl; and

R⁸ is C₆-C₁₂aryl; or C₁-C₈alkyl, or

R¹¹ and R¹¹′, R¹² and R¹²′, R¹³ and R¹³′, and R¹³′, R¹⁴, R⁴¹ and R⁴¹′ ,R⁴¹′ and R⁴³, R⁴⁴ and R⁴⁴′, R⁴⁶ and R⁴⁶′, R⁴⁶′ and R⁴⁸ and/or R⁴⁷ andR⁴⁸ are each a divalent group

In one more preferred embodiment of the present invention W, X and r areindependently of each other a group of formula

R¹¹, R¹¹′, R¹², R¹²′, R¹³, R¹³′, R¹⁵, R¹⁵′, R¹⁶, R¹⁶′, R¹⁷ and R¹⁷′ areindependently of each other H, C₆-C₁₈aryl; C₆-C₁₈aryl which issubstituted by G; E, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by Eand/or interrupted by D; C₇C₁₈aralkyl; C₇-C₁₈aralkyl which issubstituted by G; and D, E, G, R¹⁴, R¹⁸ and R¹⁹ are as defined above, or

W is a group of the formula —W¹—W²—W³,

X is a group of the formula —X¹—X²—X³ and

Y is a group of the formula —Y¹—Y²—Y³, wherein W¹, W², X¹, X², Y¹ and Y²are independently of each other a group of formula

and W³, X³ and Y³ are independently of each other a group of formula

wherein R¹⁴ is as defined above.

W, X and Y can be different, but have preferably the same meaning.

Triazine compounds of formula I are preferred, wherein R¹¹, R¹¹′, R¹²,R¹²′, R¹³, R¹³′, R¹⁵, R¹⁵′, R¹⁶, R¹⁶′, R¹⁷ and R¹⁷′, R⁴¹, R⁴¹′, R⁴²,R⁴²′, R⁴⁴, R⁴⁴′, R⁴⁵, R⁴⁵′, R⁴⁶, R⁴⁶′, R⁴⁷ and R⁴⁷′ are independently ofeach other H, E; or C₁-C₈alkyl; wherein

E is —OR⁵; —SR⁵; —NR⁵R⁶; —COR⁸; —COOR⁷; —CONR⁵R⁶; —CN; —OCOOR⁷; orhalogen; wherein R⁵ and R⁶ are independently of each other C₆-C₁₂aryl;or C₁-C₈alkyl;

R⁷ is C₇-C₁₂ alkylaryl, or C₁-C₈alkyl; and

R⁸ is C₆-C₁₂aryl, or C₁-C₈alkyl.

Especially preferred are triazine compounds of formula I, wherein W, Xand Y are independently of each other a group of formula

wherein R¹³, R¹³′, R¹⁵ and R¹⁵′ are H and R²⁰ is H, especially

R¹³ and R¹⁵ are H, R¹³′ and R¹⁵′ are independently of each other H,C₁l-C₈alkyl, or C₁-C₈alkoxy, and R²⁰ is H, C₁-C₈alkyl, or C₁-C₈alkoxy;or

R¹³, R¹⁵ and R¹⁵′ are H, R¹³′ and R²⁰ are

R₂₀, R¹⁵ and R¹⁵′ are H, and R¹³ and R¹³′ are

R³⁰, R³¹, R³² and R³³ are H, C₁-C₈alkyl, or C₁-C₈alkoxy; or wherein

W, X and Y are independently of each other a group of formula

wherein R¹⁸ and R¹⁹ are independently of each other C₁-C₈alkyl.

Specific examples of preferred triazine compounds are:

The present triazine compounds show a high solid state fluorescence inthe desired wavelength range and can be prepared according to oranalogous to known procedures. The triazine compounds of the presentinvention of the formula:

can, for example, be prepared according to a process, which comprisesreacting a derivative of formula

wherein R¹⁰⁰ stands for halogen such as chloro or bromo, preferablybromo, or E having the meaning of

wherein a is 2 or 3,

-   -   with boronic acid derivative    -   E-Ar,    -   or—in case R¹⁰⁰ is not halogen—    -   Hal-Ar,    -   wherein Hal stands for halogen, preferably for bromo,    -   wherein Ar is C₁₂-C₃₀aryl, which can be substituted, especially        in the presence of an allylpalladium catalyst of the        μ-halo(triisopropylphosphine)(η3-allyl)palladium(II) type (see        for example WO99/47474).

Accordingly, unsymmetrical substituted triazine compounds of the presentinvention of the formula:

can, for example, be prepared according to a process, which comprisesreacting a derivative of formula

with a boronic acid derivative E-Ar, wherein E is as defined above.

C₁-C₁₈alkyl is a branched or unbranched radical such as for examplemethyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl,tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl,1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl,1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl,2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl,decyl, undecyl, 1-methylundecyl, dodecyl, 1,1,3,3,5,5-hexamethylhexyl,tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, or octadecyl.

C₁-C₁₈Alkoxy radicals are straight-chain or branched alkoxy radicals,e.g. methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy,tert-butoxy, amyloxy, isoamyloxy or tert-amyloxy, heptyloxy, octyloxy,isooctyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tetradecyloxy,pentadecyloxy, hexadecyloxy, heptadecyloxy and octadecyloxy.

C₂-C₁₈Alkenyl radicals are straight-chain or branched alkenyl radicals,such as e.g. vinyl, allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl,isobutenyl, n-penta-2,4-dienyl, 3methyl-but-2-enyl, n-oct-2-enyl,n-dodec-2-enyl, isododecenyl, n-dodec-2-enyl or n-octadec4-enyl.

C₂₋₂₄Alkynyl is straight-chain or branched and preferably C₂₋₈alkynyl,which may be unsubstituted or substituted, such as, for example,ethynyl, 1-propyn-3-yl, 1-butyn-4-yl, 1-pentyn-5-yl,2-methyl-3-butyn-2-yl, 1,4-pentadiyn-3-yl, 1,3-pentadiyn-5-yl,1-hexyn-6-yl, cis-3-methyl-2-penten-4n-1-yl,trans-3-methyl-2-penten-4-yn-1-yl, 1,3-hexadiyn-5-yl, 1-octyn-8-yl,1-nonyn-9-yl, 1-decyn-10-yl or 1-tetracosyn-24-yl, C₄-C₁₈cycloalkyl ispreferably C₆-C₁₂cycloalkyl, such as, for example, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl,cyclododecyl. Cyclohexyl and cyclododecyl are most preferred.

The term “aryl group” is typically C₆-C₃₀aryl, such as phenyl, indenyl,azulenyl, naphthyl, biphenyl, terphenylyl or quadphenylyl, as-indacenyl,s-indacenyl, acenaphthylenyl, phenanthryl, fluoranthenyl, triphenlenyl,chrysenyl, naphthacen, picenyl, perylenyl, pentaphenyl, hexacenyl,pyrenyl, or anthracenyl, preferably phenyl, 1-naphthyl, 2-naphthyl,9-phenanthryl, 2- or 9-fluorenyl, 3- or 4-biphenyl, which may beunsubstituted or substituted. Examples of C₆-C₁₈aryl are phenyl,1-naphthyl, 2-naphthyl, 3- or 4-biphenyl, 9-phenanthryl, 2- or9-fluorenyl, which may be unsubstituted or substituted.

C₇-C₂₄aralkyl radicals are preferably C₇-C₁₈aralkyl radicals, which maybe substituted, such as, for example, benzyl, 2-benzyl-2-propyl,β-phenyl-ethyl, α,α-dimethylbenzyl, ω-phenyl-butyl,ω,ω-dimethyl-ω-phenyl-butyl, ω-phenyl-dodecyl, ω-phenyl-octadecyl,ω-phenyl-eicosyl or ω-phenyl-docosyl, preferably C₇-C₁₈aralkyl such asbenzyl, 2-benzyl-2-propyl, β-phenyl-ethyl, α,α-dimethylbenzyl,ω-phenyl-butyl, ω,ω-dimethyl-ω-phenyl-butyl, ω-phenyl-dodecyl orω-phenyl-octadecyl, and particularly preferred C₇C₁₂aralkyl such asbenzyl, 2-benzyl-2-propyl, β-phenyl-ethyl, α,α-dimethylbenzyl,ω-phenyl-butyl, or ω,ω-dimethyl-ω-phenyl-butyl, in which both thealiphatic hydrocarbon group and aromatic hydrocarbon group may beunsubstituted or substituted.

C₇-C₁₂alkylaryl is, for example, a phenyl group substituted with one,two or three C₁-C₈alkyl groups, such as, for example, 2-, 3-, or4-methylphenyl, 2-, 3-, or 4-ethylphenyl, 3-, or 4-isopropylphenyl,3,4-dimethylphenyl, 3,5-dimethylphenyl, or 3,4,5-trimethylphenyl.

The term “heteroaryl group”, especially C₂-C₃₀heteroaryl, is a ring,wherein nitrogen, oxygen or sulfur are the possible hetero atoms, and istypically an unsaturated heterocyclic radical with five to 18 atomshaving at least six conjugated π-electrons such as thienyl,benzo[b]thienyl, dibenzo[b,d]thienyl, thianthrenyl, furyl, furfuryl,2H-pyranyl, benzofuranyl, isobenzofuranyl, 2H-chromenyl, xanthenyl,dibenzofuranyl, phenoxythienyl, pyrrolyl, imidazolyl, pyrazolyl,pyridyl, bipyridyl, triazinyl, pyrimidinyl, pyrazinyl, 1 H-pyrrolizinyl,isoindolyl, pyndazinyl, indolizinyl, isoindolyl, indolyl, 3H-indolyl,phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl,indazolyl, purinyl, quinolizinyl, chinolyl, isochinolyl, phthalazinyl,naphthyridinyl, chinoxalinyl, chinazolinyl, cinnolinyl, pteridinyl,carbazolyl, 4aH-carbazolyl, carbolinyl, benzotriazolyl, benzoxazolyl,phenanthrldinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl,isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl or phenoxazinyl,preferably the above-mentioned mono- or bicyclic heterocyclic radicals,which may be unsubstituted or substituted.

Halogen is fluorine, chlorine, bromine and iodine.

Examples of a five or six membered ring formed by R⁵ and R⁶ areheterocycloalkanes or heterocycloalkenes having from 3 to 6 carbon atomswhich can have one additional hetero atom selected from nitrogen, oxygenand sulfur, for example

which can be part of a bicyclic system, for example

Possible substituents of the above-mentioned groups are C₁-C₈alkyl, ahydroxyl group, a mercapto group, C₁-C₈alkoxy, C₁-C₈alkylthio, halogen,halo-C₁-C_(*)alkyl, a cyano group, an aldehyde group, a ketone group, acarboxyl group, an ester group, a carbamoyl group, an amino group, anitro group or a silyl group.

As described above, the aforementioned radicals may be substituted by Eand/or, if desired, interrupted by D. Interruptions are of coursepossible only in the case of radicals containing at least 2 carbon atomsconnected to one another by single bonds; C₆-C₁₈aryl is not interrupted;interrupted arylalkyl or alkylaryl contains the unit D in the alkylmoiety. C₁-C₁₈alkyl substituted by one or more E and/or interrupted byone or more units D is, for example, (CH₂CH₂O)_(n)—R^(x), where n is anumber from the range 1-9 and R^(x) ^(H or C) ₁-C₁₀alkyl orC₂z-C₁₀alkanoyl (e.g. CO—CH(C₂H₅)C₄H₉), CH₂—CH(OR^(y)′)—CH₂—O—R^(y),where R^(y) is C₁-C₁₈alkyl, C₆-C₁₂cycloalkyl, phenyl, C₇-C₁₆phenylalkyl,and R^(y) embraces the same definitions as R^(y) or is H;C₁-C₈alkylene-COO—R^(z), e.g. CH₂COOR_(z), CH(CH₃)COOR^(z),C(CH₃)₂COOR^(z), where R^(z) is H, C₁-C₁₈alkyl, (CH₂CH₂O)₁₋₉—R^(x), andR^(x) embraces the definitions indicated above; CH₂CH₂—O—CO—CH═CH₂;CH₂CH(OH)CH₂—O—CO—C(CH₃)═CH₂.

The electroluminescent devices may be employed for full color displaypanels in, for example, mobile phones, televisions and personal computerscreens.

The following Examples illustrate the invention. In the Examples andthroughout this application, the term light emitting material means thepresent triazine compounds.

EXAMPLES Example 1

In a 25 ml three necked vessel equipped with a reflux condenser, anargon inlet and a thermometer, 0.5 g2,4,6-tris-(4-bromophenyly)-3,5-triazine [synthesized according toHayami S., Inoue K, Chem. Letters, (1999), (7), 545-546] and 0.816 g4-biphenylboronic acid are added to 10 ml of toluene under argon. Then asolution of 2.238 g CsCO₃ in 3.5 ml water is added, and 1% of apalladium(II)catalyst [described in WO99/47474] is added. Then themixture is heated to reflux for 3 hours. The product is filtered andwashed with acetone. Then the product is recrystallized fromdimethylformamide. The fine crystals are washed with isopropanol anddried. 0.51 g of pure product (A1) are obtained. Melting point: 360° C.

¹H NMR (CDCl₃, 300 MHz): δ=8.91 (6H), 7.89 (6H), 7.82 (6H), 7.75 (6H),7.68 (6H), 7.49 (6H), 7.40 (3H).

Example 2

A solution of 28.3 g (0.120 mol) p-dibromo-benzene in 90 mlterahydrofurane (THF) is added dropwise under nitrogen to 3.21 g (0.132mol) of magnesium in 10 ml diethyl ether. The p-dibromo-benzene solutionis added in a way that the reaction mixture keeps refluxing. After theaddition of the p-dibromo-benzene solution the reaction mixture isstirred for 1 h. This solution is then added to a solution of 5.53 g (30mmol) of cyanuric chloride in 50 ml THF. The reaction mixture is stirredfor 5 h at 20° C. and then hydrolysed with water and 20% hydrochloricacid. The water phase is extracted with dichloromethane. The organicphase is dried with magnesium sulfate and filtered on silica gel withdichloromethane. The solvent is removed in vacuum. Afterrecrystallisation in toluene 2.1 g (4.93 mmol; yield 16%) of the productare obtained.

Example 3

1.72 g (8.75 mmol) phenylbronic acid are added to 1.06 g (2.5 mmol)1,3-bis-(-p-bromophenyl)-5-chloro-triazine in 50 ml dimethoxyethane(DME) under argon. To this solution 2.85 g (8.75 mmol) Cs₂CO₃ in 5 mlwater and 1% of a palladium(II)catalyst [described in WO99/47474] areadded. The reaction mixture is refluxed for 18 h and then diluted withwater. The product is filtered off, washed with 20% hydrochloric acidand then water. After recrystallisation in DMF 1.1 g (1.59 mmol; yield64%) of the product are obtained.

Application Example

Present compound Al, as light emitting material,2,5-bis(1-naphthylyl,3,4-oxadiazole and a polycarbonate resin in aweight ratio of 5:3:2 are dissolved in tetrahydrofuran, and the solutionis spin-coated on a cleaned glass substrate with an ITO electrode toform a light-emitting layer having a thickness of 100 nm. An electrodehaving a thickness of 150 nm is formed thereon from a magnesium/indiumalloy having a magnesium/indium mixing ratio of 10/1, to obtain anorganic EL device. The device exhibits light emission with excellentbrightness and efficiency at a direct current voltage of 5 V.

Application Example 2

Present compound A1 is vacuum-deposited on a cleaned glass substratewith an ITO electrode to form a light-emitting layer having a thicknessof 100 nm. An electrode having a thickness of 100 nm is formed thereonfrom a magnesium/silver alloy having a magnesium/silver mixing ratio of10/1, to obtain an organic EL device. The light-emitting layer is formedby deposition under a vacuum of 10⁻⁶ Torr at a substrate temperature ofroom temperature. The device shows emission having an excellentbrightness and efficiency at a direct current voltage of 5 V.

Application Example 3

Present compound Al is dissolved in methylene chloride tetrahydrofuran,and the solution is spin-coated on a cleaned glass substrate with an ITOelectrode to form a light-emitting layer having a thickness of 50 nm.Then, aluminum bis(2-methyl4l-quinolinate)(2-naphtolate) isvacuum-deposited to form an electron transporting layer having athickness of 10 nm, and an electrode having a thickness of 100 nm isformed thereon from a magnesium/aluminum alloy having amagnesium/aluminum mixing ratio of 10/1, to obtain an organic EL device.The light-emitting layer and the electron-injecting layer are formed bydeposition under a vacuum of 10⁻⁶ Torr at a substrate temperature ofroom temperature. The device shows an emission having an excellentbrightness and efficiency at a direct current voltage of 5 V.

Application Example 4

One of hole transporting materials (H-1) to (H-6) is vacuum-deposited ona cleaned glass substrate with an ITO electrode, to form a holetransporting layer having a thickness of 30 nm. Then, present compoundA1 is vacuum-deposited to form a light-emitting layer having a thicknessof 30 nm. Further, one of electron transporting materials (E-1) to (E-6)is vacuum-deposited to form an electron transporting layer having athickness of 30 nm. An electrode having a thickness of 150 nm is formedthereon from a magnesium/silver alloy having a magnesium/silver mixingratio of 10/1, to obtain an organic EL device. Each layer is formedunder a vacuum of 10⁶ Torr at a substrate temperature of roomtemperature. All the organic EL devices obtained in these Examples showshigh brightness and efficiency.

Application Example 5

On a cleaned glass substrate with an ITO electrode,4,4′,4″-tris(N-(3-methylphenyl)-N-phenylamino)triphenylamine isvacuum-deposited to form a hole-injecting layer having a thickness of 25nm. Further, a hole transporting material (H-1) is vacuum-deposited toform a hole transporting layer having a thickness of 5 nm. Then,compound Al as light-emitting material is vacuum-deposited to form alight-emitting layer having a thickness of 20 nm. Further, an electrontransporting material (E-1) is vacuum-deposited to form an electrontransporting layer having a thickness of 30 nm. Then, an electrodehaving a thickness of 150 nm is formed thereon from a magnesium/silveralloy having an magnesium/silver mixing ratio of 10/1, to obtain anorganic EL device. The device shows emission having an outstandingbrightness and efficiency at a direct current voltage of 5 V.

Application Example 6

A hole transporting material (H-5) is vacuum-deposited on a cleanedglass substrate with an ITO electrode to form a hole transporting layerhaving a thickness of 20 nm. Then, compound A1 as light-emittingmaterial is vacuum-deposited to form a light-emitting layer having athickness of 20 nm. Further, an electron transporting material (E-2) isvacuum-deposited to form a first electron transporting layer having athickness of 20 nm. Then, an electron transporting material (E-5) isvacuum-deposited to form a second electron transporting layer having athickness of 10 nm, and an electrode having a thickness of 150 nm isformed thereon from a magnesium/silver alloy having an magnesium/silvermixing ratio of 10/1, to obtain an organic EL device. The device showslight emission having an excellent brightness and efficiency at a directcurrent voltage of 5 V.

Application Example 7

An organic EL device is prepared in the same manner as in Example 4except that the light-emitting layer is replaced with a 30 nm thicklight-emitting layer formed by vacuum-depositing compound A1 and one ofthe dopant compounds (D-1) to (D-7) in a weight ratio of 100:1. All theorganic EL devices obtained in these Examples shows high brightnesscharacteristics and gives intended light emission colors.

Application Example 8

On a cleaned glass substrate with an ITO electrode,N,N′-1-naphthyl-N,N′-diphenyl-1,1′-biphenyl-4,4′-diamine and5,10-diphenylanthracene are vacuum-deposited to form a hole-injectinglayer. Further, 4,4′-bis(9-carbazolyl)-1,1′-biphenyl is vacuum-depositedto form a hole transporting layer. Then, compound A1 as light-emittingmaterial is vacuum-deposited to form a light-emitting layer. Then, anelectrode is formed thereon from a magnesium/silver alloy having anmagnesium/silver mixing ratio of 9/1, to obtain an organic EL device.The device shows emission having an outstanding brightness andefficiency at a direct current voltage of 5 V.

The organic EL devices obtained in the Application Examples of thepresent invention show an excellent light emission brightness andachieved a high light emission efficiency. When the organic EL devicesobtained in the above Examples are allowed to continuously emit light at3 (mA/cm²), all the organic EL devices remain stable. Since thelight-emitting materials of the present invention have a very highfluorescence quantum efficiency, the organic EL devices using thelight-emitting materials achieved light emission with a high brightnessin a low electric current applied region, and when the light-emittinglayer additionally uses a doping material, the organic EL devices areimproved in maximum light emission brightness and maximum light emissionefficiency. Further, by adding a doping material having a differentfluorescent color to the light-emitting material of the presentinvention, there are obtained light-emitting devices having a differentlight emission color. The organic EL devices of the present inventionaccomplish improvements in light emission efficiency and light emissionbrightness and a longer device life, and does not impose any limitationson a light-emitting material, a dopant, a hole transporting material, anelectron transporting material, a sensitizer, a resin and an electrodematerial used in combination and the method of producing the device. Theorganic EL device using the material of the present invention as alight-emitting material achieves light emission having a high brightnesswith a high light emission efficiency and a longer life as compared withconventional devices. According to the light-emitting material of thepresent invention and the organic EL device of the present invention,there can be achieved an organic EL device having a high brightness, ahigh light emission efficiency and a long life.

1. A triazine compound of formula I

W is a group of formula

X and Y are independently of each other an aryl group or a heteroarylgroup, wherein R¹¹, R¹¹′, R¹², R¹²′, R¹³, R¹³′, R¹⁵, R¹⁵′, R¹⁶, R¹⁶′,R¹⁷, and are independently of each other H, E, C₆-C₁₈aryl; C₆-C₁₈arylwhich is substituted by G; C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substitutedby E and/or interrupted by D; C₇-C₁₈aralkyl; or C₇-C₁₈aralkyl which issubstituted by G; and R¹⁴ is H, C₂-C₃₀heteroaryl, C₂-C₃₀heteroaryl,which is substituted by G, C₆-C₃₀aryl, or C₆-C₃₀aryl, which issubstituted by G, C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is substituted by Eand/or interrupted by D; or R¹¹′ and R¹², R¹²′ and R¹³, R¹⁵′ and R¹⁶,and/or R¹⁶′ and R¹⁷, are each a divalent group L¹ selected from anoxygen atom, an sulfur atom, >CR¹⁸R¹⁹>SiR¹⁸R¹⁹, or

R¹⁸ and R¹⁹ are independently of each other C₁-C₁₈alkyl; C₁-C₁₈alkoxy,C₆-C₁₈aryl; C₇-C₁₈aralkyl; R¹¹ and R¹¹′, R¹² and R¹²′, R¹³ and R¹³′,R¹³′ and R¹⁴, R¹⁴ and R¹⁵, R¹⁵ and R¹⁵′, R¹⁶ and R¹⁶′, and/or R¹⁷′ andR¹⁷, are each a divalent group

R³⁰, R³¹, R³², R³³, R⁴⁹ and R⁵⁰ are independently of each other H,C₁l-C₁₈alkyl; C₁l-C₁₈alkyl, which is substituted by E and/or interruptedby D; E; C₆-C,₈aryl; C₆-C₁₈aryl, which is substituted by E; D is —CO—;—COO—; —OCOO—; —S—; —SO—; —SO₂—; —O—; —NR⁵—; SiR⁶¹R⁶²—; —POR⁵—;—CR⁶³═CR⁶⁴—; or —C≡C—; E is —OR⁵; —SR⁵; —NR⁵R⁶; —COR⁸; —COOR⁷; —OCOOR⁷,—CONR⁵R⁶; —CN; or halogen; G is E, or C₁-C₁₈alkyl, wherein R⁵ and R⁶ areindependently of each other C₆-C₁₈aryl; C₆-C₁₈aryl which is substitutedby C₁-C₁₈alkyl, C₁-C₁₈alkoxy; or C₁-C₁₈alkyl which is interrupted by—O—; or R⁵ and R⁶ together form a five or six membered ring, R⁷ isC₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl,C₁-C₁₈alkoxy; or C₁-C₁₈alkyl which is interrupted by —O—; R⁸ isC₇-C₁₂alkylaryl; C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is interrupted by—O—; R⁶¹ and R⁶² are independently of each other C₆-C₁₈aryl; C₆-C₁₈arylwhich is substituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy; or C₁-C₁₈alkyl whichis interrupted by —O—, and R⁶³ and R⁶⁴ are independently of each otherH, C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl,C₁-C₁₈alkoxy; or C₁-C₁₈alkyl which is interrupted by —O—.
 2. A triazinecompound of formula I according to claim 1, wherein W, X and Y areindependently of each other a group of formula

R¹¹, R¹¹′, R¹², R¹²′, R¹³, R¹³′, R¹⁵, R¹⁵′, R¹⁶, R¹⁶′, R¹⁷ and R¹⁷′areindependently of each other H, C₆-C₁₈aryl; C₆-C₁₈aryl which issubstituted by G; E, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by Eand/or interrupted by D; C₇-C₁₈aralkyl; C₇-C₁₈aralkyl which issubstituted by G; and D, E, G, R¹⁴, R₁₈ and R¹⁹ are as defined in claim1, or W is a group of the formula —W¹—W²—W³, X is a group of the formula—X¹—X²—X³ and Y is a group of the formula —Y¹—Y²—Y³, wherein W¹, W², X¹,X², Y¹ and Y² are independently of each other a group of formula

and W³, X³ and Y³are independently of each other a group of formula

wherein R¹⁴ is as defined above.
 3. The triazine compound according toclaim 1, wherein R¹¹, R¹¹′, R¹², R¹²′, R¹³, R¹³′, R¹⁵, R¹⁵′, R¹⁶, R¹⁶′,R¹⁷ and R17′ as well as R¹⁴, are independently of each other H, E; orC₁-C₈alkyl; wherein E is —OR⁵; —SR⁵; —NR⁵R⁶; —COR⁸; —COOR⁷; —CONR⁵R⁶;—CN; —OCOOR⁷; or halogen; wherein R⁵ and R⁶ are independently of eachother C₆-C₁₂aryl, or C₁-C₈alkyl; R⁷ is C₇-C₁₂alkylaryl, or C₁-C₈alkyl;and R⁸ is C₆-C₁₂aryl; or C₁-C₈alkyl.
 4. The triazine compound accordingto claim 1, wherein W, X and Y are a group of formula

R¹³, R¹³′, R¹⁵ and R¹⁵′ are H and R²⁰ is H, especially

or R¹³ and R¹⁵ are H, R¹³′ and R¹⁵′ are independently of each other H,C₁-C₈alkyl, or C₁-C₈alkoxy, and R²⁰ is H, C₁-C₈alkyl, or C₁-C₈alkoxy; orR¹³, R¹⁵ and R¹⁵′ are H, and R¹³′ and R²⁰ are

R²⁰, R¹⁵ and R¹⁵′ are H, and R¹³ and R¹³′ are

wherein R³⁰, R³¹, R³² and R³³ are H, C₁-C₈alkyl, or C₁-C₈alkoxy.
 5. Thetriazine compound according to claim 1, wherein W, X and Y areindependently of each other a group of formula

wherein R¹⁸ and R¹⁹ are independently of each other C₁-C₈alkyl.
 6. Thetriazine compound according to claim 11, wherein W and Y areindependently of each other a group of formula

and X is a group of formula

wherein R¹¹, R¹¹′, R¹², R¹²′, R¹³, R¹³′, R¹⁴, R¹⁵, R¹⁵′, R¹⁶, R¹⁶′, R¹⁷,R¹⁷′, R⁴¹, R⁴¹′, R⁴², R⁴²′, R⁴⁴, R⁴⁴′, R⁴⁵, R⁴⁵′, R⁴⁶, R⁴⁶′, R⁴⁷, R⁴⁷′,R⁴³ and R⁴⁸ are defined as in claim
 11. 7. An electroluminescent device,comprising a triazine compound of formula I according to claim
 1. 8.Electroluminescent device according to claim 7, wherein theelectroluminescent device comprises in this order (a) an anode (b) ahole injecting layer and/or a hole transporting layer (c) alight-emitting layer (d) optionally an electron transporting layer and(e) a cathode.
 9. Electroluminescent device according to claim 8,wherein the triazine compound of formula I forms the light-emittinglayer.
 10. Electrophotographic photoreceptors, photoelectric converters,solar cells, image sensors, dye lasers and electroluminescent devicescomprising a triazine compound according to claim
 1. 11. A triazinecompound according to claim 1, wherein X and Y are independently of eachother a group of formula

wherein R¹¹, R¹¹′, R¹², R¹²′, R¹³, R¹³′, R¹⁵, R¹⁵′, R¹⁶, R¹⁶′, R¹⁷,R¹⁷′, R⁴¹, R⁴¹′, R⁴², R⁴²′, R⁴⁵, R⁴⁵′, R⁴⁶, R⁴⁶′, R⁴⁷ and R⁴⁷′ areindependently of each other H, E, C₆-C₁₈aryl; C₆-C₁₈aryl which issubstituted by G; C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by Eand/or interrupted by D; C₇-C₁₈aralkyl; or C₇-Cl₈aralkyl which issubstituted by G; R¹⁴ is H, C₂-C₃₀heteroaryl, C₂-C₃₀heteroaryl, which issubstituted by G, C₆-C₃₀aryl, or C₆-C₃₀aryl, which is substituted by G,C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is substituted by E and/or interruptedby D; and R⁴³ and R⁴⁸ are independently of each other H, E; C₁-C₁₈alkyl;C₁-C₁₈alkyl, which is substituted by E and/or interrupted by D;C₂-C₃₀heteroaryl; C₂-C₃₀heteroaryl, which is substituted by G,C₇-C₁₈aralkyl; or C₇-C₁₈aralkyl which is substituted by G; or R¹¹′ andR¹², R¹²′ and R¹³, R¹⁵′ and R¹⁶, R¹⁶′ and R¹⁷, R⁴⁴′ and R⁴⁶ and/or R⁴⁵′and R⁴⁷ are each a divalent group L¹ selected from an oxygen atom, ansulfur atom, >CR¹⁸R¹⁹>SiR¹⁸R¹⁹, or

wherein R¹⁸ and R¹⁹ are independently of each other C₁-C₁₈alkyl;C₁-C₁₈alkoxy, C₆-C₁₈aryl; C₇-C₁₈aralkyl; or R¹¹ and R¹¹′, R¹² and R¹²′,R¹³ and R¹³′ and R¹⁴, R¹⁴ and R¹⁵, R¹⁵ and R¹⁵′, R¹⁶ and R¹⁶′, R′ andR¹⁷, R⁴¹ and R⁴¹′ and R⁴² and R⁴²′, R⁴²′ and R⁴³, R⁴⁴ and R⁴⁴′, R⁴⁵ andR⁴⁵, R⁴⁶ and R⁴⁶′, R⁴⁷ and R^(47′, R) ⁴⁶′ and R⁴⁸ and/or R⁴⁷′ and R⁴⁸are each a divalent group

wherein R³⁰, R³¹, R³², R³³, R⁴⁹ and R⁵⁰ are independently of each otherH, C₁-C₁₈alkyl; C₁-C₁₈alkyl, which is substituted by E and/orinterrupted by D; E; C₆-C₁₈aryl; C₆-C₁₈aryl, which is substituted by E;D is —CO—; —COO—; —OCOO—; —S—; —SO—; —SO₂—; —O—; —NR⁵—; SiR⁶¹R⁶²—;—POR⁵—; —CR⁶³=CR⁶⁴—; or —C≡C—; E is —OR⁵; —SR⁵; —NR⁵R⁶; —COR⁸; —COOR⁷;—OCOOR⁷, —CONR⁵R⁶; —CN; or halogen; G is E, or C₁-C₁₈alkyl, wherein R⁵and R⁶ are independently of each other C₆-C₁₈aryl; C₆-C₁₈aryl which issubstituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy; or C₁-C₁₈alkyl which isinterrupted by —O—; or R⁵ and R⁶together form a five or six memberedring, R⁷ is C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl,C₁-C₁₈alkoxy; or C₁-C₁₈alkyl which is interrupted by —O—; R⁸ isC₇-C₁₂alkylaryl; C₁-C₁₈alkyl; or C₁-C₁₈alkyl which is interrupted by—O—; R⁶¹ and R⁶² are independently of each other C₆-C₁₈aryl; C₆-C₁₈arylwhich is substituted by C₁-C₁₈alkyl, C₁-C₁₈alkoxy; or C₁-C₁₈alkyl whichis interrupted by —O—, and R⁶³ and R⁶⁴ are independently of each otherH, C₆-C₁₈aryl; C₆-C₁₈aryl which is substituted by C₁-C₁₈alkyl,C₁-C₁₈alkoxy; or C₁-C₁₈alkyl which is interrupted by —O—.
 12. A triazinecompound according to claim 11, wherein R¹⁴ is

wherein R²¹, R²², R²³, R²⁴, R²⁵, R²⁶ and R²⁷ are independently of eachother H, E, C₁-C₁₈alkyl; C₁-C₁₈alkyl which is substituted by E and/orinterrupted by D; E; C₇-C₁₈aralkyl; C₇-C₁₈aralkyl which is substitutedby G and does not form a divalent group with R^(—)′ or R¹⁵, R¹⁵.
 13. Atriazine compound according to claim 11, wherein R⁵ and R⁶ together form


14. A triazine compound according to claim 11 wherein R¹¹, R¹¹′, R¹²,R¹²′, R¹³, R¹³′, R¹⁵, R¹⁵′, R¹⁶, R¹⁶′, R¹⁷ and R¹⁷′, R⁴¹, R⁴¹′, R⁴²,R⁴²′, R⁴⁴, R⁴⁴′, R⁴⁵, R⁴⁵′, R⁴⁶, R⁴⁶′, R⁴⁷, and R⁴⁷′ as well as R¹⁴,R⁴³, and R⁴⁸ are independently of each other H, E, or C₁-C₈alkyl;wherein E is —OR⁵; —SR⁵; —NR⁵R⁶; —COR⁸; —COOR⁷, —CONR⁵R⁶; —CN, —OCOOR⁷,or halogen; R⁵ and R⁶ are independently of each other C₆-C₁₂aryl, orC₁-C₈alkyl; R⁷ is C₇-C₁₂alkylaryl, or C₁-C₈alkyl; and R⁸ is C₆-C₁₂aryl;or C₁-C₈alkyl.
 15. The triazine compound according to claim 6, whereinR¹¹, R¹¹′, R¹², R¹²′, R¹³, R¹³′, R¹⁴, R¹⁵, R¹⁵′, R¹⁶, R¹⁶′, R¹⁷, R¹⁷′,R⁴¹, R⁴¹′, R⁴², R⁴²′, R⁴⁴, R⁴⁴′, R⁴⁵, R⁴⁵′, R⁴⁶, R⁴⁶′, R⁴⁷, R⁴⁷′, R⁴³and R⁴⁸ are are H, C₁-C₈alkyl, C₁-C₈alkoxy, or phenyl.
 16. The triazinecompound according to claim 15, wherein W and Y are independently ofeach other a group of formula

X is a group of formula